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Aryl-diyne linkers in bis-triarylborane cations control fluorimetric and Raman sensing of various DNA and RNA

Ferger, Matthias; Ban, Željka; Krošl, Ivona; Tomić, Sanja; Dietrich, Lena; Lorenzen, Sabine; Rauch, Florian; Sieh, Daniel; Friedrich, Alexandra; Griesbeck, Stefaine; Kenđel, Adriana; Miljanić, Snežana; Piantanida, Ivo; Marder, Todd B. (2021) Aryl-diyne linkers in bis-triarylborane cations control fluorimetric and Raman sensing of various DNA and RNA. Chemistry : a European journal, 27 . pp. 5142-5159. ISSN 0947-6539

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Abstract

We report four new luminescent tetracationic bis-triarylborane DNA and RNA sensors that show high binding affinities, in several cases even in the nM range. Three of the compounds contain substituted, highly emissive, and structurally flexible bis(2, 6-dimethylphenyl-4- ethynyl)arene linkers (3: arene = 5, 5’-2, 2’-bithiophene ; 4: arene = 1, 4-benzene ; 5: arene = 9, 10-anthracene) between the two boryl moieties and serve as efficient dual Raman and fluorescence chromophores. The shorter analogue 6 employs bis(2, 6- dimethylphenyl)-9, 10-anthracene as the linker and demonstrates the importance of an adequate linker length with a certain level of flexibility by exhibiting generally lower binding affinities than 3-5. Pronounced aggregation - deaggregation processes are observed in fluorimetric titration experiments with DNA for compounds 3 and 5. Molecular modelling of complexes of 5 with AT-DNA, suggest the minor 2 groove as the dominant binding site for monomeric 5, but demonstrate that dimers of 5 can also be accommodated. Strong SERS responses for 3-5 (particularly compound 5) vs. a very weak response for 6 demonstrate the importance of triple bonds for strong Raman activity in molecules of this compound class. The energy of the characteristic stretching vibration of the C≡C bonds is significantly dependent on the aromatic moiety between the triple bonds. The insertion of aromatic moieties between two C≡C bonds thus offers an alternative design for dual Raman and fluorescence chromophores, applicable in multiplex biological Raman imaging.

Item Type: Article
Uncontrolled Keywords: Borane ; Fluorescent probe ; Raman probe ; DNA/RNA Sensor ; Molecular Modelling
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteinaPiantanida, IvoIP-2018-01-5475HRZZ
Depositing User: Ivo Piantanida
Date Deposited: 24 Mar 2021 12:59
Last Modified: 24 Mar 2021 12:59
URI: http://fulir.irb.hr/id/eprint/6357
DOI: 10.1002/chem.202005141

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